Manufacture of acetyl derivatives of the alkylated iminopyrimidins.



T all wh'oni i t may concern:

' UNITED STATES PATENT OFFICE.

ERHARD WITTE, 0F GItOSS-LICHTERFELDE. NEAR .BERLIN, GERMANY, ASSIGNQR TO CHEMISCHE FABRIK AUF ACTIEN (VORM. E. SCHERING,) 0F BERLIN, GERMANY.

lllANUF-AC'I'URE oF ACETYL DEBIVATIVES OF THE ALKYLATED IMINOP YRIMTDINS.

No Drawing.

Be it known that I. Ennann Vrrrn, doctor of philosophy, chemist, citizen of the Get man Empire residing at Gross-Lichterfelde, near Berlin, German Empire, have invented a new and useful Improvement in the Mannfacture of AcetylDerivatives of the Alkylated Iniinopyrimidins, of which the. following is a specification.

I According to this invention the hitherto unknown acetyl derivatives of the alkylated iminopyrimidins are obtained, corresponding to the formula in which w is meant for a hydrogen atom or alkyl, 3 signifies O or NH or NCOCH but one y always represents N.C()Cl-l..

At a lower temperature the reaction takgs place more slowly, at a higher temperature more quickly. .The acetyl deriyative melts about 176 centigrade. 'It dissolves in glacial acetic acid and acetic anhydrid and can be recrystallized from alcohol.

is produced which decomposes on heating to about 240 centigrade. Like the acetyl compound itself the hydrochlorid is transformed by treatment with water into the corresponding alkylbarbiturie acid.

3. 10 parts by weight of 5-dipropyl-2- imino-.4,6-dioxypyrimidin are heated to the boil with 40 parts by weight of anhydrous acetic acid. 'On cooling the 5-dipropyl-2- acetylimino 4,6- dioxypyrimidin separates Specification of Letters Patent.

\Vhen the resulting solu-' PatentedFeb. 18, 1913.

Application filed August 23, 1905. Serial No. 514,228.

The compounds are colorless, odorless and tasteless. they are soluble in concentrated alcohol and when mixed with water or aqueous acids split otl'the acetyl group and are transformed into the corresponding alkyl barbituric acid.

These ace'tyl derivatives are obtained by treatingthe alkylated iminopyrimidins with acetylating agents.

Examples.

parts by weight'ot' anhydrous acetic acid for about three hours a-t to centigrade.

Theresulting 'solutiomis 'lliltered off from any nnpuritles and on cooling the 5 diethyl- Q-acety htu1no-4,G-dlpxypyrimidin separates out in fine crystals. The reaction takes place in accordance with the following equation:

out from the solution produced in beautiful crystals. The melting point of the compound crystallized from alcohol or glacial acetic acid or anhydrous acetic acid -.is about 184 to 186 centigrade. a

4. 1.8 parts by weight of 5-diethyl-2,4- diimino-6-oxypyrimidin are heated to the boil with 5 parts by weight vof anhydrous acetic acid. .l.he'melting point of the 5- dicthyl 2,4 diacetylinlino 6 oxypyrimidin which separates from the resulting solution on cooling is about 136 to 138 centigrade.

Forthe purpose of acetylization the 5- diethyl-2,4=-diimino-6-oxypyrimidin may also be heated to the boil with 5 parts ofglacial acetic acid. a little-.moretha'n' the theoretical quantity of anhydrous acetic acid being then added. In this case also 5-diethyl-2,4-diacetylimino-G-oXypyrimidin is produced. T

5. 1.5 parts by weight of 5-monoethyl-2- imino-etfi-dioxypyrimidin are heated with 3 parts by Weight of'anhydrous acetic acid to the boil. The acetylization is hastened by the addition of a small quantity of concentrated sulfuric acid. The 5-mono-ethyl-2- 'acetylimino 4,6 dioxypyrimidin separates out on cooling in fine flat. crystals, which on recrysta lizatiou from alcohol begin to melt at about 202 centigrade.

The higher homologues of the last mentioned compounds can be obtained in a similar manner and also the acetyl compounds of the dins (the 5-diethyl4-acetylimino-2,6-dioxypyrimidin melts when crystallized from strong alcohol at about 158 to 159 cent-igrade) and of the alkylated triiminopyrimidin.

The herein described new chemical com pounds have soporific properties and can be used as soporifics or hypnotics, or they may be employed for the production of dialkylated barbituric acid. a

I claim, as my invention:

1. The herein described new chemical compounds which are the acetyl derivatives of the alkylated'iminopyrimidins and are colorless, odorless and tasteless substances, soluble in concentrated alcohol, and are converted into the corresponding alkyl barbituric acids by the action of Water or aqueous acids. I

5-dialkyl-Limino-2,6rdioxypyrimi- I my signature in dins, which consists (3) (4), N +00, 2)0001; Nd h u 3= 2/ I v 5 i l' 2 5 1 H-CO being soluble in concentrated alcohol, glacial acetic acid and acetic anhydrid,'and being converted into diethylbarbituric acidby the act-ion of Water or aqueous acids.

3. The process of manufacturing the acetyl derivatives of alkylated iminopyriming agent to act upon alkylated iminopyr unidins andfisolating the formed acetyl dcrivatiye,substantially as described.

In test-unony whereof I have hereunto the presence at two an? scribing witnesses. H

ERHABTD W I "lilE. /Vitnesses:

HENRY HAsPnR," VVOLDEMAR HAUPT.

in causing an acetylat 

